[1]孙 松,徐圣博.铑催化芳甲酰乙腈与硫叶立德氧化环化合成多取代萘/2,3-二氢苯并色烯[J].常州大学学报(自然科学版),2019,31(03):23-33.[doi:10.3969/j.issn.2095-0411.2019.03.002]
 SUN Song,XU Shengbo.Rholdium-Catalyzed Cascade Oxidative Annulation of Benzoylacetonitriels by Sulfoxonium Ylides Leading to Substituted Naphthalenes/Benzo[de]Chromenes[J].Journal of Changzhou University(Natural Science Edition),2019,31(03):23-33.[doi:10.3969/j.issn.2095-0411.2019.03.002]
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铑催化芳甲酰乙腈与硫叶立德氧化环化合成多取代萘/2,3-二氢苯并色烯()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
第31卷
期数:
2019年03期
页码:
23-33
栏目:
化学化工
出版日期:
2019-05-28

文章信息/Info

Title:
Rholdium-Catalyzed Cascade Oxidative Annulation of Benzoylacetonitriels by Sulfoxonium Ylides Leading to Substituted Naphthalenes/Benzo[de]Chromenes
文章编号:
2095-0411(2019)03-0023-11
作者:
孙 松徐圣博
(常州大学 石油化工学院,江苏 常州 213164)
Author(s):
SUN Song XU Shengbo
(School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China)
关键词:
铑催化 环化 芳甲酰乙腈 硫叶立德 多取代萘 苯并色烯
Keywords:
Key words:rhodium catalysis annulation benzoylacetonitriles sulfoxonium ylides substituted naphthalenes benzo[de]chromenes
分类号:
O 625.11
DOI:
10.3969/j.issn.2095-0411.2019.03.002
摘要:
研究了铑(III)催化芳甲酰乙腈与硫叶立德的[4+2]环化反应,合成了一系列的多取代萘甲腈,且该反应产率较高和官能团适应性好。该反应可能经历了连续的铑(III)插入碳-氢键、还原消除和环化反应。在此过程中,硫叶立德作为一种高效的卡宾前体。另外,当硫叶立德的用量提高到两倍物质的量时,所得产物主要是苯并色烯。
Abstract:
Rh(III)-catalyzed [4+2]-annulation of benzoylacetonitriles with sulfoxonium ylides was developed to access substituted naphthalenes in moderate to excellent yields with good functional group compatibilities. This procedure proceeded with the sequential insertion of the Rh(III)carbene to the C-H bond, reductive elimination and cyclization steps, where sulfoxonium ylides served as an efficient and stable carbene precursor. Notably, benzo[de]chromenes were formed in the presence of two equivalents of sulfoxonium ylides.

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备注/Memo

备注/Memo:
收稿日期:2018-03-20。
基金项目:国家自然科学基金资助项目(20160129); 江苏省自然科学基金资助项目(BK20150263)。
作者简介:孙松(1985—),男,江苏扬州人,博士,讲师。E-mail:sunsong@cczu.edu.cn
更新日期/Last Update: 2019-05-29